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Synthesis 2022; 54(12): 2885-2893
DOI: 10.1055/a-1777-2423
DOI: 10.1055/a-1777-2423
paper
Stereoselective Synthesis of Dispirooxindoles Incorporating Pyrrolo[2,1-a]isoquinoline via [3+2] Cycloaddition of Azomethine Ylides with a Thiazolo[3,2-a]indole Dipolarophile
N.V.T thanks the University Grants Commission (UGC) for the financial support in terms of Senior research fellowship and M.C.B and S.S.L thank University of Kerala for Junior research fellowships.
Abstract
Highly regio- and stereoselective synthesis of dispiropyrrolo[2,1-a]isoquinoline-oxindoles have been developed by the one-pot three component reaction of isatins, 1,2,3,4-tetrahydroisoquinoline (THIQ), and a thiazolo[3,2-a]indole derivative. The reaction proceeds regioselectively through an exo-Re face approach of the in situ generated tetrahydroisoquinolium ylides towards the dipolarophile yielding the corresponding [3+2] cycloadducts in excellent yields and stereoselectivity.
Key words
[3+2] cycloaddition - azomethine ylide - 1,2,3,4-tetrahydroisoquinoline - thiazolo[3,2-a]indole - spiropyrrolo[2,1-a]isoquinolineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1777-2423.
- Supporting Information
Publication History
Received: 18 February 2022
Accepted after revision: 21 February 2022
Accepted Manuscript online:
21 February 2022
Article published online:
05 April 2022
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